EP3452220A1 - Système de synthèse chimique à étapes multiples reconfigurable et composants et procédés associés - Google Patents

Système de synthèse chimique à étapes multiples reconfigurable et composants et procédés associés

Info

Publication number
EP3452220A1
EP3452220A1 EP17793166.4A EP17793166A EP3452220A1 EP 3452220 A1 EP3452220 A1 EP 3452220A1 EP 17793166 A EP17793166 A EP 17793166A EP 3452220 A1 EP3452220 A1 EP 3452220A1
Authority
EP
European Patent Office
Prior art keywords
fluidic
bay
module
fiuidic
connection
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP17793166.4A
Other languages
German (de)
English (en)
Other versions
EP3452220A4 (fr
Inventor
Andrea Adamo
Dale Arlington THOMAS III
Klavs F. Jensen
Timothy F. Jamison
Aaron A. BEDERMANN
Kosisochukwu C. AROH
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Massachusetts Institute of Technology
Original Assignee
Massachusetts Institute of Technology
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Massachusetts Institute of Technology filed Critical Massachusetts Institute of Technology
Publication of EP3452220A1 publication Critical patent/EP3452220A1/fr
Publication of EP3452220A4 publication Critical patent/EP3452220A4/fr
Withdrawn legal-status Critical Current

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0053—Details of the reactor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J14/00—Chemical processes in general for reacting liquids with liquids; Apparatus specially adapted therefor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0006—Controlling or regulating processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0006—Controlling or regulating processes
    • B01J19/004—Multifunctional apparatus for automatic manufacturing of various chemical products
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/24—Stationary reactors without moving elements inside
    • B01J19/245—Stationary reactors without moving elements inside placed in series
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00051—Controlling the temperature
    • B01J2219/00054—Controlling or regulating the heat exchange system
    • B01J2219/00056—Controlling or regulating the heat exchange system involving measured parameters
    • B01J2219/00058—Temperature measurement
    • B01J2219/00063—Temperature measurement of the reactants
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00162—Controlling or regulating processes controlling the pressure
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00164—Controlling or regulating processes controlling the flow
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00177—Controlling or regulating processes controlling the pH
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00186—Controlling or regulating processes controlling the composition of the reactive mixture
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00277—Apparatus
    • B01J2219/00279—Features relating to reactor vessels
    • B01J2219/00306—Reactor vessels in a multiple arrangement
    • B01J2219/00308—Reactor vessels in a multiple arrangement interchangeably mounted in racks or blocks
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
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    • B01J2219/00277—Apparatus
    • B01J2219/00351—Means for dispensing and evacuation of reagents
    • B01J2219/00418—Means for dispensing and evacuation of reagents using pressure
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00277—Apparatus
    • B01J2219/00479—Means for mixing reactants or products in the reaction vessels
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00783—Laminate assemblies, i.e. the reactor comprising a stack of plates
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00801—Means to assemble
    • B01J2219/0081—Plurality of modules
    • B01J2219/00813—Fluidic connections
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00801—Means to assemble
    • B01J2219/0081—Plurality of modules
    • B01J2219/00815—Electric connections
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00819—Materials of construction
    • B01J2219/00822—Metal
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00819—Materials of construction
    • B01J2219/00833—Plastic
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00819—Materials of construction
    • B01J2219/00835—Comprising catalytically active material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00851—Additional features
    • B01J2219/00867—Microreactors placed in series, on the same or on different supports
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00873—Heat exchange
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00889—Mixing
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00905—Separation
    • B01J2219/00907—Separation using membranes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • B01J2219/00925—Irradiation
    • B01J2219/00934—Electromagnetic waves
    • B01J2219/00936—UV-radiations
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    • B01J2219/00925—Irradiation
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    • B01J2219/00945—Infrared light
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    • B01J2219/0095—Control aspects
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01L—CHEMICAL OR PHYSICAL LABORATORY APPARATUS FOR GENERAL USE
    • B01L3/00—Containers or dishes for laboratory use, e.g. laboratory glassware; Droppers
    • B01L3/50—Containers for the purpose of retaining a material to be analysed, e.g. test tubes
    • B01L3/502—Containers for the purpose of retaining a material to be analysed, e.g. test tubes with fluid transport, e.g. in multi-compartment structures
    • B01L3/5027—Containers for the purpose of retaining a material to be analysed, e.g. test tubes with fluid transport, e.g. in multi-compartment structures by integrated microfluidic structures, i.e. dimensions of channels and chambers are such that surface tension forces are important, e.g. lab-on-a-chip
    • B01L3/502715—Containers for the purpose of retaining a material to be analysed, e.g. test tubes with fluid transport, e.g. in multi-compartment structures by integrated microfluidic structures, i.e. dimensions of channels and chambers are such that surface tension forces are important, e.g. lab-on-a-chip characterised by interfacing components, e.g. fluidic, electrical, optical or mechanical interfaces

Definitions

  • Such arrangements may be achieved, for example, by connecting second fluidic connection 108B of second bay 104B to first fluidic connection 106C of third bay 104C, for example, with a fluidic channel.
  • the fluidic distributor can be configured such that the first bay is coupled to a module in which a first step of a chemical synthesis process is performed, the second bay is coupled to a module in which a second step of the chemical synthesis process is performed (after the first step), and the third bay is coupled to a module in which a third step of the chemical synthesis process is performed (after the first and second steps).
  • the first fluidic connection of the third bay can be configured to transport fluid out of the fluidic distributor via the third bay (e.g., into a module coupled to the third bay).
  • first fluidic connection 106C of third bay 104C can be configured to transport fluid out of fluidic distributor 102 via third bay 104C into a module coupled to third bay 104C.
  • the second fluidic connection of the third bay can be configured to transport fluid into the fluidic distributor via the third bay (e.g., from a module coupled to the third bay).
  • second fluidic connection 108C of third bay 104C can be configured to transport fluid into fluidic distributor 102 via third bay 104C from a module coupled to third bay 104C.
  • the clamp may comprise fluidic connections and/or electrical interfaces on one or more surfaces.
  • FIG. IE shows an example of a top surface of a bay that is a clamp and comprises a first fluidic connection and a second fluidic connection.
  • clamp 114E comprises first fluidic connection 106E and second fluidic connection 108E.
  • these fluidic connections may couple with first and second fluidic connections on module 150E.
  • each fluidic connection may be on the same surface of the clamp as shown in FIG. IE (such as a surface on which an electrical interface is located, or a surface on which an electrical interface is not located), or the fluidic connections may be present on two or more surfaces of the clamp.
  • the surface(s) may be interior surface(s) of the clamp, and/or surface(s) of the clamp that are configured to abut an external surface of a module.
  • one or more of the modules described herein can comprise a non-reactor unit operation.
  • the non-reactor unit operation can be any type of unit operation that is not a reactor.
  • the non-reactor unit operation is a separator.
  • the non-reactor unit operation is a mixer.
  • the computer implemented control system(s) also may include one or more input devices.
  • Example input devices include a keyboard, keypad, track ball, mouse, pen and tablet, communication devices such as described above, and data input devices such as audio and video capture devices and sensors.
  • the computer implemented control system(s) is not limited to the particular input or output devices described herein.
  • modules comprising reactors may comprise a metal plate comprising a groove that houses tubing (e.g., perfluorinated polymer tubing).
  • tubing e.g., perfluorinated polymer tubing
  • such tubing may be made into preforms which may provide ease of operation.
  • the tubing may be manually laid into the groove in certain embodiments.
  • the tubing may be disposable and/or low cost.
  • an automated fluidic system may allow the user to treat the system as a black box. Automation of a fluidic system may be accomplished by a variety of suitable automation systems. In certain embodiments, automation may be accomplished by the use of a software program such as Labview.
  • face plate 450 may house device components such as switches, IR sensors 470A-E, and outlet ports 490A, 490B, and 490C. Face plate 450 may be fabricated from sheet metal in some embodiments. In some embodiments, a cover is attached to face plate 450 by hinge 475.
  • outlet ports 490A-C may comprise outlets for product and/or waste.
  • This example describes the use of a fluidic system to perform a Friedel-Crafts Acylation, a reaction which is used to form greater than 10% of all carbon-carbon bonds in process chemistry.
  • the Friedel-Crafts Acylation was performed in a fluidic system comprising 1 bay, 2 pumps, and a heated reactor.
  • Anisole and butyric acid in a trifluoroacetic anhydride and phosphoric acid solution were introduced into a first module at 50 °C. Upon exiting the module, the product 4'-methoxybuterophenone was recovered at a conversion efficiency greater than 90%.
  • FIG. 33 displays a schematic of the reaction setup.
  • This example describes the use of a fluidic system to perform a
  • This example describes the use of a fluidic system to perform a Suzuki coupling reaction, which is used to form approximately 40% of carbon-carbon bonds in medicinal chemistry and is the most common cross-coupling reaction used in medicinal chemistry.
  • the Suzuki coupling reactions were performed in a reactor comprising 1 bay, 2 pumps, and a packed bed reactor.
  • Aryl-X in THF and a solution comprising phenylboronic acid, sodium hydroxide, water, and ethanol was added to a SS Packed Bed Column at 70 °C comprising SiliaCat DPP-Pd. After 12 minutes, the reagents exited the module. The conversion was assessed using crude GC analysis with an internal standard. The desired product was achieved with a conversion ranging from 81% to 99% depending upon the identity of Aryl-X.
  • FIG. 37 displays a schematic of the reaction setup, including possible conversions which were obtained from different combinations of reagents.
  • This example describes the use of a fluidic system to perform B-Alkyl Suzuki couplings.
  • the B-Alkyl Suzuki couplings were performed in a fluidic system
  • a 0.2 M solution of tri ethyl phosphonoacetate was mixed with a 1 M solution of potassium tert-butoxyde in THF. The mixed solutions were held at 50 °C for 5 minutes. The resulting stream was then mixed with a 0.2 M solution of 4-phenylcyclohexanone in THF and held at 70 °C for 5min. At the conclusion of the reaction, the desired product was obtained in 65% yield.
  • FIG. 48 displays a schematic of the reaction setup.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Physical Or Chemical Processes And Apparatus (AREA)

Abstract

La présente invention concerne des distributeurs fluidiques, des systèmes fluidiques et des procédés et articles associés. Certains modes de réalisation concernent des distributeurs fluidiques qui comprennent des compartiments comprenant des connexions fluidiques ayant des positions relatives qui correspondent sensiblement les unes aux autres. Selon certains modes de réalisation, un distributeur fluidique peut comprendre des compartiments avec des interfaces électriques ayant des positions relatives qui correspondent sensiblement les unes aux autres.
EP17793166.4A 2016-05-02 2017-05-02 Système de synthèse chimique à étapes multiples reconfigurable et composants et procédés associés Withdrawn EP3452220A4 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201662330769P 2016-05-02 2016-05-02
PCT/US2017/030649 WO2017192595A1 (fr) 2016-05-02 2017-05-02 Système de synthèse chimique à étapes multiples reconfigurable et composants et procédés associés

Publications (2)

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EP3452220A1 true EP3452220A1 (fr) 2019-03-13
EP3452220A4 EP3452220A4 (fr) 2020-01-01

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US (1) US11185839B2 (fr)
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WO (1) WO2017192595A1 (fr)

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JP6787881B2 (ja) 2014-08-15 2020-11-18 マサチューセッツ インスティテュート オブ テクノロジー 有効医薬品原料を含む化学生成物を合成するためのシステムおよび方法
WO2018200236A1 (fr) 2017-04-26 2018-11-01 Massachusetts Institute Of Technology Systèmes et procédés de synthèse chimique reconfigurables
GB201718917D0 (en) 2017-11-16 2018-01-03 Ge Healthcare Bioprocess R&D Ab Method and system for manufacturing of biopharmaceutical products
US20210331170A1 (en) * 2020-04-22 2021-10-28 Quantum-Si Incorporated Terminal functionalization of target molecules for sequencing

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